Substituted 2,1,3-benzothiadiazine compounds

ABSTRACT

New and valuable substituted 2,1,3-benzothiadiazine compounds having a good herbicidal action, herbicides containing these active ingredients, methods of controlling the growth of unwanted plants with these compounds, and processes for manufacturing them.

The present invention relates to new and valuable substituted 2,1,3-benzothiadiazine compounds having a good herbicidal action, herbicides containing these active ingredients, and methods of controlling the growth of unwanted plants with these compounds.

It is known that 3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide and 1-methyl-3-isopropyl-8-methyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide have a herbicidal action (German Pat. No. 1,542,836, German Laid-Open Application DOS No. 2,443,901).

We have now found that compounds of the formula ##STR1## WHERE R¹ denotes alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkoxyalkyl, alkylmercaptoalkyl, alkyl- and dialkylcarbamoylalkyl, alkoxycarbonyl, alkoxycarboalkyl, alkoxycarboalkenyl, dialkylketone, unsubstituted aryl, aryl substituted by halogen, methyl and/or halomethyl, or R¹ denotes a heterocyclic ring, R² denotes the radicals CN, SCN, ##STR2## C(═N--OR⁴)R³, S(O)_(k) R³, S(═O)OR³, S(═O)₂ OR³, Si(R⁶)₂ R⁷, ##STR3## or SCCl₂ F, X denotes halogen, NO₂, lower alkyl, halo lower alkyl, cycloalkyl, arylalkyl, aryl, CN, SCN, CO₂ R³, ##STR4## Y'R⁴, SO₂ R³, SO₂ OR³, ##STR5## CCl₃, CF₃, C(═O)R³ or Y"CF₂ C(Z)₃, R³ denoting hydrogen, lower alkyl, unsubstituted aryl, or aryl substituted by halogen, methyl or nitro, R⁴ and R⁵ being identical or different and each having the meanings of R³ and additionally denoting, but not simultaneously, dialkylketone, R⁶ and R⁷ being identical or different and each having the meanings of R³ with the exception of hydrogen, R⁸ and R⁹ being identical or different and each having the meanings of R³ with the exception of hydrogen and aryl, A having the meanings of R³ or denoting OR³, N(R³)₂, OC(═O)NHR³ or OC(═O)R³, each Y, Y' and Y" independently denoting oxygen or sulfur, each Z independently denoting hydrogen, fluorine, bromine, chlorine or iodine, and k denoting one of the integers 0 and 1, m denotes one of the integers 0, 1, 2, 3 and 4, and n denotes one of the integers 1 and 2, are good herbicides which, particularly as selective herbicides, have a superior action to prior art compounds.

The new benzothiadiazine compounds of the formula 1 are obtained by reacting compounds of the formula ##STR6## where R¹, X, Y, m and n have the above meanings, with a halogen compound of the formula

    Hal--R.sup.2                                               3,

where R² has the above meanings and Hal denotes a halogen atom, in the presence or absence of an acid binder and of an inert solvent, or by reacting salts of compounds of the formula 2 with halogen compounds in the presence or absence of an inert solvent. The starting compounds of the formula 2 are obtained by known methods, for example from substituted anthranilic acid derivatives and substituted sulfamic acid halides. A 1CN derivative obtained in this manner may if desired be further reacted with hydroxylamine.

Examples of meanings for R¹ are: hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert.-butyl, cyclobutyl, n-pentyl, 2-pentyl, 3-pentyl, tert.-amyl, neopentyl, 2-methylbutyl, 3-methylbutyl, 3-methyl-2-butyl, cyclopentyl, n-hexyl, 4-methyl-2-pentyl, 2,3-dimethylbutyl, 2-methyl-1-pentyl, 2-hexyl, 3-hexyl, 3-methyl-2-pentyl, 3-methylpentyl, 4-methylpentyl, 3-methyl-3-pentyl, 4,4-dimethylbutyl, cyclohexyl, heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-octyl, 2-octyl, 3-octyl, 4-octyl, 5-octyl, 5-ethyl-2-heptyl, 2,6-dimethyl-4-heptyl, 7-ethyl-2-methyl-4-nonyl, 2,4-dimethyl-3-pentyl, 3-methyl-2-heptyl, 5-ethyl-2-nonyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentydecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, 6-ethyl-3-decyl, 6-ethyl-3-octyl, 2-methyl-2-pentyl, 2,3-dimethyl-2-butyl, 2-methyl-2-hexyl, 3-ethyl-3-pentyl, 3-methyl-3-hexyl, 2,3-dimethylpentyl-3, 2,4-dimethyl-2-pentyl, 2,2,3-trimethyl-3-butyl, 2-methyl-2-heptyl, 4-methyl-4-heptyl, 2,4-dimethyl-2-hexyl, 2-methyl-2-octyl, 1-methyl-1-cyclopentyl, 1-methyl-1-cyclohexyl, 1-ethyl-1-cyclohexyl, chloro-tert.-butyl, 1,1-dichloro-2-methyl-2-propyl, 1,3-dichloro-2-methyl-2-propyl, 1-cyclohexyl-1-ethyl, 1-chloroethyl, 2-chloroethyl, 1-chloropropyl, 2-chloropropyl, 3-chloropropyl, 1-chloro-2-propyl, 2-chlorobutyl, 2-chloro-2-methyl-3-propyl, 1-fluoroethyl, 2-fluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 1-fluoro-2-propyl, 2-fluorobutyl, 2-fluoro-2-methyl-3-propyl, 2-bromoethyl, 3-bromopropyl, 4-chlorobutyl, 2-chlorocyclohexyl, 1,1,1-trifluoroisopropyl, hexafluoro-2-methylisopropyl, hexafluoroisopropyl, hexachloroisopropyl, 1,2-dibromoallyl, 2,2,2-trifluoroethyl, 1-chlorobutyn-2-yl-4, 3-chloro-butyn-1-yl-4, 1-chlorobuten-2-yl-4, 2,3-dibromo-1-propyl, 2,2,2-trichloroethyl, 1-chloropentyn-2-yl-4, 2,2,2-tribromoethyl, 3,4,4-trichlorobuten-3-yl-2, 1-bromo-2-propyl, 1,3-dibromo-2-propyl, 3-chlorobuten-1-yl-4, allyl, methallyl, crotyl, 2-ethylhexen-2-yl-1, hexen-5-yl-1, undecen-10-yl-1, 2-methylbuten-2-yl-1, 2-methylbuten-1-yl-3, butyn-1-yl-3, butyn-2-yl-1, buten-1-yl-3, propargyl, 2-methylbuten-1-yl-4, 2-methylbuten-2-yl-4, 3-methylbuten-1-yl-3, 1-ethynylcyclohexyl, methoxyethyl, ethoxyethyl, 3-methoxypropyl, methoxyisopropyl, 3-methoxybutyl, 1-methoxybutyl-2, ethoxy-tert.-butyl, methoxy-tert.-butyl, cyclohexoxytert.-butyl, 2-methoxybutyl, 4-methoxybutyl, methylmercaptoethyl, ethylmercaptoethyl, 3-methylmercaptopropyl, 3-methylmercaptobutyl, 1-methylmercaptobutyl-2, methylmercapto-tert.-butyl, 2-methylmercaptobutyl, 4-methylmercaptobutyl, 3-n-butoxyethyl, 2-ethoxypropyl, 3-ethoxy-2-propyl, 2-methylbutanon-3-yl-2, 2-methylpentanon-4-yl-2, 3-butanon-1-yl, 3-butanon-2-yl, 2-propanon-1-yl, 2-pentanon-1-yl, methyl acetate-2, ethyl acetate-2, methyl propionate-2, methyl propionate-3, methyl butyrate-2, methyl butyrate-3, methyl butyrate-4, methyl-(2-vinyl propionate-2), methyl-(2-vinyl acetate-2), methylcarbamoylmethyl, dimethylcarbamoylmethyl, phenyl, o-tolyl, m-tolyl, p-fluorophenyl, m-fluorophenyl, p-chlorophenyl, p-tolyl, o-chlorophenyl, o,p-dichlorophenyl, o,p-difluorophenyl, m-trifluoromethylphenyl, o-fluorophenyl, 3,5-dimethylphenyl, 3,5-dichlorophenyl, p-bromophenyl, m-bromophenyl, 3,5-difluorophenyl and pyrrolidinyl.

Examples of meanings for R² are: cyano, thiocyanato, guanyl, N² -methylguanyl, N² -ethylguanyl, N¹ -ethyl-N¹ -methyl-N² -phenylguanyl, N¹ -methylguanyl, N¹ -isopropylguanyl, N¹,N¹ -dimethylguanyl, N¹,N¹, N² -trimethylguanyl, N² -hydroxyguanyl, N² -methoxyguanyl, N¹ -isopropyl-N² -methoxyguanyl, N¹ -methyl-N¹ -propyl-N² -methoxyguanyl, N² -methylcarbamoyloxyguanyl, N² -acetoxyguanyl, N¹,N¹ -dimethyl-N² -acetoxyguanyl, N¹,N¹ -dimethyl-N² -aminoguanyl, N¹,N¹ -dimethyl-N² -dimethylaminoguanyl, methanecarbohydroximoyl, benzohydroximoyl, ethanecarbohydroximoyl, O-methylbenzohydroximoyl, O-ethylethanecarbohydroximoyl, O-propylmethanecarbohydroximoyl, amino, dimethylamino, diethylamino, N-isopropyl-N-methylamino, N-ethyl-N-butylamino, methylamino, isopropylamino, sec-butylamino, α-methylpiperidino, methylsulfenyl, ethylsulfenyl, p-chlorophenylsulfenyl, 2,4-dinitrophenylsulfenyl, p-tolylsulfenyl, dichlorofluoromethylsulfenyl, methoxysulfynyl, ethoxysulfynyl, benzyloxysulfynyl, methoxysulfonyl, ethoxysulfonyl, N-methoxymethyl-N-methylsulfamoyl, N-isopropyl-N-methoxymethylsulfamoyl, N-sec-butyl-N-methoxymethylsulfamoyl and trimethylsilyl.

The term "halogen" denotes fluorine, chlorine, bromine and iodine. The terms "lower alkyl" and "halo lower alkyl" denote linear or branched, optionally halogen-substituted alkyl of from 1 to 6 carbon atoms.

The term "cycloalkyl" denotes for instance cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. The term "aryl" denotes phenyl and substituted phenyl, such as halophenyl or tolyl.

If the starting materials are 3-phenyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide and cyanogen bromide, the reaction according to the invention may be represented by the following scheme: ##STR7##

If the starting materials are the sodium salt of 3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide and N-methoxymethyl-N-methylsulfamoyl chloride, the reaction may be represented by the following scheme: ##STR8##

If the starting materials are 1-cyano-3-methyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide and hydroxylamine hydrochloride, the reaction may be represented by the following scheme: ##STR9##

In a preferred embodiment, for instance a 3-alkyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide is reacted with a halogen derivative of the formula 3, in the presence or absence of an inert solvent and of an acid binder at from -50° to +120° C., preferably from -20° to +50° C., for from 1 to 20 hours, continuously or batchwise, and at atmospheric or superatmospheric pressure.

Examples of preferred inert solvents in the process of the invention are hydrocarbons such as ligroin, gasoline, toluene, pentane, hexane, cyclohexane and petroleum ether; halohydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,1- and 1,2-dichloroethane, 1,1,1- and 1,1,2-trichloroethane, chlorobenzene, o,m,p-dichlorobenzene and o,m,p-chlorotoluene; nitrohydrocarbons such as nitrobenzene, nitroethane and o,m,p-chloronitrobenzene; nitriles such as acetonitrile, butyronitrile, isobutyronitrile and benzonitrile; ethers such as diethyl ether, di-n-propyl ether, tetrahydrofuran and dioxane; esters such as acetoacetic ester, ethyl acetate and isobutyl acetate; amides such as formamide, methyl formamide and dimethyl formamide; and ketones such as acetone, butanone-2, acetophenone and cyclohexanone. For the reaction with hydroxylamine, alcohols, e.g., ethanol, isopropanol or butanol, may also be used.

The following compounds, for example, may be used as acid binders: sodium carbonate, sodium bicarbonate, triethylamine, pyridine, trimethylamine, α,β,γ-picoline, lutidine, N,N-dimethylaniline, N,N-dimethylcyclohexylamine, quinoline, tri-n-propylamine, n-propyldiisopropylamine and tri-n-butylamine.

Starting materials 2 and 3 may be added in any order. Instead of employing an acid binder, it is possible to remove the hydrogen halide formed during the reaction with an inert gas, e.g., nitrogen. The following procedure is particularly preferred. A solution or suspension of starting material 3 in one of the abovementioned inert solvents is run into a solution or suspension of starting material 2, or a salt thereof, in one of the abovementioned inert solvents; alternatively, starting material 3 is introduced undiluted into the solution or suspension of starting material 2 in one of the abovementioned inert solvents, the acid binder, either undiluted or diluted with one of the abovementioned inert solvents, is then run in, and the reaction carried out in the prescribed temperature range.

In addition to the 2,1,3-benzothiadiazine derivatives of the formula 2, the alkali metal, alkaline earth metal, ammonium or zinc salts derived therefrom may be used as starting materials. The halogen derivatives 3 are advantageously employed in amounts of from 1 to 4, preferably from 1.2 to 1.4, moles per mole of starting compound 2.

To isolate the compounds of the formula 1 from the reaction mixture in accordance with the invention, the reaction mixture is stirred--when water-miscible solvents are used--into a dilute aqueous alkali metal solution. The oil which separates out is if desired extracted and the extract is washed with water and dried. If water-immiscible solvents are used, the reaction mixture may also be extracted direct with dilute alkali metal solution and water. If desired, the reaction mixture may also be concentrated, taken up in a water-immiscible solvent and worked up as described above. The desired end products are obtained by drying and concentrating the organic phase. If desired, they may be further purified in conventional manner, e.g., by recrystallization or chromatography.

EXAMPLE 1

22.6 parts (by weight) of 3-ethyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide was dissolved in 100 parts of acetone; while stirring and at 0° C., 12 parts of cyanogen bromide was added and then 11.5 parts by weight of triethylamine was dripped in. The reaction mixture was stirred for 8 hours at 0° C. and for 12 hours at room temperature, the precipitate was filtered off and the organic phase concentrated. 300 parts of methylene chloride was added and extraction carried out twice with 100 parts of 1 N aqueous caustic solution and once with water. After drying over magnesium sulfate, concentration and recrystallization from isopropanol, 18 parts (71% of theory) of 1-cyano-3-ethyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide was obtained as colorless crystals; m.p.: 89°-91° C.

EXAMPLE 2

At room temperature and while stirring, 12 parts of cyanogen bromide was added to a suspension of 27.8 parts of the potassium salt of 3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide in 300 parts of acetonitrile. After the reaction mixture had been stirred for 20 hours, it was concentrated, poured into 300 parts of water, and extracted with 200 parts of methylene chloride. The organic extract was washed with saturated sodium bicarbonate solution, dried and concentrated. 1-cyano-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide, m.p. 100°-101° C., was obtained by recrystallization from isopropanol.

EXAMPLE 3

22.6 parts of 3-ethyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide was dissolved in 150 parts of ethyl acetate; at 20° C., 15 parts of cyanogen bromide and then 14 parts of triethylamine were added. After the mixture had been stirred for 3 hours at room temperature, it was filtered and the filtrate was extracted twice with cold 1 N aqueous caustic soda solution. After drying, the solvent was removed and the residue recrystallized from isopropanol. There was obtained 21.3 parts (85% of theory) of 1-cyano-3-ethyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide; m.p.: 89°-91° C.

EXAMPLE 4

7.7 parts of hydroxylamine hydrochloride and 12 parts of anhydrous sodium carbonate were suspended in 300 parts of absolute ethanol and stirred for 30 minutes at room temperature. While cooling, 26.5 parts of 1-cyano-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide was introduced and the whole stirred for 4 hours at room temperature. After the reaction mixture had been filtered and concentrated, the residue was dissolved in 500 parts of ethyl acetate and extracted twice with saturated bicarbonate solution. The organic phase was dried, concentrated and recrystallized from toluene; there was obtained 1-(N² -hydroxy)-guanyl-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide having a melting point of 175° C. (decomposes).

EXAMPLE 5

24 parts of 3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide was suspended in 150 parts of 1,2-dichloroethane; at 5° to 10° C., 12 parts of cyanogen bromide was added. At this temperature, 14 parts of N,N-dimethylcyclohexylamine was then dripped in and the mixture stirred for 4 hours at room temperature. The solution was then washed twice with cold 1 N aqueous caustic soda solution and once with water, and dried, and the solvent was removed in vacuo. After recrystallization from isopropanol, there was obtained 22 parts (83% of theory) of pure 1-cyano-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide, m.p.: 100°-101° C.

EXAMPLE 6

At 0° C., 22.6 parts of 3-ethyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide was introduced into a solution of 7 parts of cyanogen chloride in 200 parts of 1,2-dichloroethane. 14 parts of N,N-dimethylcyclohexylamine was then dripped in and the mixture was stirred for 3 hours at room temperature. Subsequently, the mixture was washed twice with cold 1 N aqueous caustic soda solution and once with water, and dried, and the solvent was removed in vacuo. After recrystallization from isopropanol, there was obtained 22 parts (88% of theory) of 1-cyano-3-ethyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide; m.p.: 90°-91° C.

Further active ingredients of the formula 1 were prepared analogously. They are listed in the following table, m denoting 0.

                                      TABLE 1                                      __________________________________________________________________________     R.sup.1              R.sup.2        Y n m.p.(°C.)                       __________________________________________________________________________     CH.sub.3             CN             O 2 102-103                                CH.sub.3             SCN            O 2                                        CH.sub.3             C(NOH)NH.sub.2 O 2                                        CH.sub.3             C(NH)N(CH.sub.3).sub.2                                                                        O 2                                        CH.sub.3             C(NOCOCH.sub.3)NH.sub.2                                                                       O 2                                        CH.sub.3             C(NOH)C.sub.2 H.sub.5                                                                         O 2                                        CH.sub.3             SO.sub.2 OCH.sub.3                                                                            O 2                                        CH.sub.3             Si(CH.sub.3).sub.3                                                                            O 2                                        CH.sub.3             C(NOCH.sub.3)NH.sub.2                                                                         O 2                                        CH.sub.3             NH.sub.2       O 2                                        CH.sub.3             N(CH.sub.3).sub.2                                                                             O 2                                        CH.sub.3             SC.sub.6 H.sub.4 -p-Cl                                                                        O 2                                        CH.sub.3             SCCl.sub.2 F   O 2                                        CH.sub.3             CN             S 2                                        CH.sub.3             CN             O 1                                        CH.sub.3                                                                                             ##STR10##     O 2                                        C.sub.2 H.sub.5                                                                                      ##STR11##     O 2                                        C.sub.2 H.sub.5      SO.sub.2 OCH.sub.3                                        C.sub.2 H.sub.5      SC.sub.6 H.sub.3 -2,4(NO.sub.2).sub.2                                                         O 2                                        C.sub.2 H.sub.5      SCCl.sub.2 F   O 2 n .sub.D.sup.23 =                                                              1.5545                                 C.sub.2 H.sub.5      NH.sub.2       O 2                                        C.sub.2 H.sub.5      NH-i-C.sub.3 H.sub.7                                                                          O 2                                        C.sub.2 H.sub.5      C(NH)N(CH.sub.3).sub.2                                                                        O 2                                        C.sub.2 H.sub.5      C(NOCH.sub.3)NH.sub.2                                                                         O 2                                        C.sub.2 H.sub.5      C(NOCH.sub.3)C.sub.6 H.sub.5                                                                  O 2                                        C.sub.2 H.sub.5      CN             S 2                                        C.sub.2 H.sub.5      CN             O 1                                        C.sub.2 H.sub.5      SCN            O 2                                        n-C.sub.3 H.sub.7    SCN            O 2                                        n-C.sub.3 H.sub.7    NH.sub.2       O 2                                        n-C.sub.3 H.sub.7    SCCl.sub.2 F   O 2                                        n-C.sub.3 H.sub.7    C(NOH)NH.sub.2 O 2                                        n-C.sub.3 H.sub.7    C(NOCOCH.sub.3)NH.sub.2                                                                       O 2                                        n-C.sub.3 H.sub.7    C(NOCH.sub.3)NHCH.sub.3                                                                       O 2                                        n-C.sub.3 H.sub.7                                                                                    ##STR12##     O 2                                        n-C.sub.3 H.sub.7    C(NOH)C.sub.6 H.sub.5                                                                         O 2                                        n-C.sub.3 H.sub.7    Si(CH.sub.3).sub.3                                                                            O 2                                        n-C.sub.3 H.sub.7    CN             O 2 97-98                                  i-C.sub.3 H.sub.7    CN             S 2                                        i-C.sub.3 H.sub.7    CN             O 1                                        i-C.sub.3 H.sub.7    SCN            O 2                                        i-C.sub.3 H.sub.7    C(NH)N(CH.sub.3).sub.2                                                                        O 2                                        i-C.sub.3 H.sub.7    C(NCH.sub.3)N(CH.sub.3).sub.2                                                                 O 2                                        i-C.sub.3 H.sub.7    C(NC.sub.2 H.sub.5)NHC.sub.3 H.sub.7                                                          O 2                                        i-C.sub.3 H.sub.7    C(NOCOCH.sub.3)NH.sub.2                                                                       O 2                                        i-C.sub.3 H.sub.7    C(NOCH.sub.3)NH.sub.2                                                                         O 2 123                                    i-C.sub.3 H.sub.7    C(NOH)N(CH.sub.3).sub.2                                                                       O 2                                        i-C.sub.3 H.sub.7                                                                                    ##STR13##     O 2                                        i-C.sub.3 H.sub.7    C(NOCONHCH.sub.3)NH.sub.2                                                                     O 2 203-204                                i-C.sub.3 H.sub.7    C(NOH)C.sub.6 H.sub.5                                                                         O 2                                        i-C.sub.3 H.sub.7    NH.sub.2       O 2                                        i-C.sub.3 H.sub.7    NH.sub.2       S 2                                        i-C.sub.3 H.sub.7    N(CH.sub.3).sub.2                                                                             O 2                                        i-C.sub.3 H.sub.7                                                                                    ##STR14##     O 2                                        i-C.sub.3 H.sub.7    SCCl.sub.2 F   O 2 NMR (CDCl.sub.3) :                                                             CH.sub.3 δ   1.55; 1.6;                                                  CH 5.05;                                                                       arom. H 7.2-8.25                       i-C.sub.3 H.sub.7    SC.sub.6 H.sub.4 -p-Cl                                                                        O 2                                        i-C.sub.3 H.sub.7    SC.sub.6 H.sub.3 -2,4(NO.sub.2).sub.2                                                         O 2                                        i-C.sub.3 H.sub.7    S(O)OC.sub.2 H.sub.5                                                                          O 2                                        i-C.sub.3 H.sub.7    S(O)OCH.sub.3  O 2                                        i-C.sub.3 H.sub.7    SO.sub.2 OCH.sub.3                                                                            O 2                                        i-C.sub.3 H.sub.7                                                                                    ##STR15##     O 2 119-123                                i-C.sub.3 H.sub.7                                                                                    ##STR16##     O 2                                        i-C.sub.3 H.sub.7                                                                                    ##STR17##     O 2                                        i-C.sub.3 H.sub.7    Si(CH.sub.3).sub.3                                                                            O 2                                        i-C.sub.3 H.sub.7    Si(C.sub.6 H.sub.5).sub.3                                                                     O 2                                        i-C.sub.3 H.sub.7    Si(C.sub.6 H.sub.5).sub.2 CH.sub.3                                                            O 2                                        n-C.sub.4 H.sub.9    SC.sub.6 H.sub.4 -p-Cl                                                                        O 2                                        n-C.sub.4 H.sub.9    SCCl.sub.2 F   0 2                                        n-C.sub.4 H.sub.9    SCN            O 2                                        n-C.sub.4 H.sub.9    CN             O 2                                        n-C.sub.4 H.sub.9    C(NOH)NH.sub. 2                                                                               O 2                                        n-C.sub.4 H.sub.9                                                                                    ##STR18##     O 2                                        n-C.sub.4 H.sub.9    C(NOCH.sub.3)C.sub.2 H.sub.5                                                                  O 2                                        n-C.sub.4 H.sub.9    NH.sub.2       O 2                                        n-C.sub.4 H.sub.9    C(NH)NHCH.sub.3                                                                               O 2                                        sec C.sub.4 H.sub.9  CN             O 2 79-80                                  sec C.sub.4 H.sub.9  CN             S 2                                        sec C.sub.4 H.sub.9  SCN            O 2                                        sec C.sub.4 H.sub.9  SCCl.sub.2 F   O 2                                        sec C.sub.4 H.sub.9  C(NOH)C.sub.6 H.sub.5                                                                         O 2                                        sec C.sub.4 H.sub.9  C(NOH)NH.sub.2 O 2 141-143                                sec C.sub.4 H.sub.9  NH.sub.2       O 2                                        CH(C.sub.2 H.sub.5).sub.2                                                                           CN             O 2                                        CH(C.sub.2 H.sub.5).sub.2                                                                           CN             O 1                                        i-C.sub.3 H.sub.7                                                                                    ##STR19##     O 2 N .sub.D.sup.25  = 1.5300              CH(C.sub.2 H.sub.5).sub.2                                                                           SCN            O 2                                        CH(C.sub.2 H.sub.5).sub.2                                                                           C(NOCH.sub.3)NH.sub.2                                                                         O 2                                        CH(C.sub.2 H.sub.5).sub. 2                                                                          C(NCH.sub.3)NH.sub.2                                                                          O 2                                        CH(C.sub.2 H.sub.5).sub.2                                                                           S(O)OC.sub.2 H.sub.5                                                                          O 2                                        CH(C.sub.2 H.sub.5).sub.2                                                                           SCCl.sub.2 F   S 2                                        CH(C.sub.2 H.sub.5).sub.2                                                                           SCCl.sub.2 F   O 2                                        CH(C.sub.2 H.sub.5).sub.2                                                                           NH.sub.2       O 2                                        CH(C.sub.2 H.sub.5).sub.2                                                                            ##STR20##     O 2                                        CH(C.sub.2 H.sub.5).sub.2                                                                           Si(CH.sub.3).sub.3                                                                            O 2                                        CH(C.sub.2 H.sub.5).sub.2                                                                            ##STR21##     O 2                                        CH(C.sub.2 H.sub.5).sub.2                                                                           C(NOH)C.sub.2 H.sub.5                                                                         O 2                                         ##STR22##           CN             O 2 118-120                                 ##STR23##           C(NOH)NH.sub.2 O 2                                         ##STR24##           SC.sub.2 H.sub.5                                                                              O 2                                         ##STR25##           SO.sub.2 OCH.sub.3                                                                            O 2                                         ##STR26##           NH.sub.2       O 2                                         ##STR27##                                                                                           ##STR28##     O 2                                         ##STR29##           C(NOH)C.sub.2 H.sub.5                                                                         O 2                                         ##STR30##           NH.sub.2       O 2                                         ##STR31##           CN             O 2                                         ##STR32##           SCN            O 2                                         ##STR33##           S(O)OCH.sub.3  O 2                                         ##STR34##           SCCl.sub.2 F   O 2                                         ##STR35##           C(NOCH.sub.3)NH.sub.2                                                                         O 2                                         ##STR36##           Si(CH.sub.3).sub.3                                                                            O 2                                         ##STR37##           C(NOH)C.sub.6 H.sub.5                                                                         O 2                                         ##STR38##           CN             O 2 116-118                                 ##STR39##           CN             S 2                                         ##STR40##           SCN            O 2                                         ##STR41##           C(NH)N(CH.sub.3).sub.2                                                                        O 2                                         ##STR42##           C(NOCH.sub.3)NH.sub.2                                                                         O 2                                         ##STR43##           SCCl.sub.2 F   O 1                                         ##STR44##           SC.sub.6 H.sub.3 -2,4(NO.sub. 2).sub.2                                                        O 2                                         ##STR45##           SO.sub.2 OC.sub.2 H.sub.5                                                                     O 2                                         ##STR46##                                                                                           ##STR47##     O 2                                         ##STR48##           NH.sub.2       O 2                                         ##STR49##           C(NOH)C.sub.6 H.sub.5                                                                         O 2                                         ##STR50##           Si(CH.sub.3).sub.3                                                                            O 2                                         ##STR51##                                                                                           ##STR52##     O 2                                         ##STR53##           S(O)OC.sub.2 H.sub.5                                                                          O 2                                         ##STR54##           SCCl.sub.2 F   O 1                                         ##STR55##           SCCl.sub.2 F   O 2                                         ##STR56##           SC.sub.6 H.sub.4 -p-CH.sub.3                                                                  O 2                                         ##STR57##                                                                                           ##STR58##     O 2                                         ##STR59##           N(CH.sub.3).sub.2                                                                             O 2                                         ##STR60##           NH.sub.2       O 2                                         ##STR61##           C(NOH)NH.sub.2 O 2                                         ##STR62##           CN             O 2                                         ##STR63##           SCN            O 2                                        CH.sub.2 CH.sub.2 Cl CN             O 2 139-140                                CH.sub.2 CH.sub.2 Cl SCN            O 2                                        CH.sub.2 CH.sub.2 Cl C(NH)NHCH.sub.3                                                                               O 2                                        CH.sub.2 CH.sub.2 Cl CN             S 2                                        CH.sub.2 CH.sub.2 Cl CN             O 1                                        CH.sub.2 CH.sub.2 Cl                                                                                 ##STR64##     O 2                                        CH.sub.2 CH.sub.2 Cl C(NOH)NH.sub.2 O 2                                        CH.sub.2 CH.sub.2 Cl NH.sub.2       O 2                                        CH.sub.2 CH.sub.2 Cl                                                                                 ##STR65##     O 2                                        CH.sub.2 CH.sub.2 Cl SCCl.sub.2 F   S 2                                        CH.sub.2 CH.sub.2 Cl SCCl.sub.2 F   O 2                                        CH.sub.2 CH.sub.2 Cl S(O)OCH.sub.3  O 2                                        CH.sub.2 CH.sub.2 Cl                                                                                 ##STR66##     O 2                                        CH.sub.2 CH.sub.2 Cl C(NOCH.sub.3)C.sub.6 H.sub.5                                                                  O 2                                         ##STR67##           CN             O 2                                         ##STR68##           SCN            O 2                                         ##STR69##           C(NOCH.sub.3)NH.sub.2                                                                         O 2                                         ##STR70##           C(NOH)NH.sub.2 O 2                                         ##STR71##           C(NH)N(CH.sub.3).sub.2                                                                        O 2                                         ##STR72##           NH.sub.2       O 2                                         ##STR73##           NH-i-C.sub.3 H.sub.7                                                                          O 2                                         ##STR74##           SCCl.sub.2 F   O 1                                         ##STR75##           SCCl.sub.2 F   O 2                                         ##STR76##           S(O)OCH.sub.3  O 2                                         ##STR77##           SO.sub.2 OC.sub.2 H.sub.5                                                                     O 2                                         ##STR78##                                                                                           ##STR79##     O 2                                         ##STR80##           Si(CH.sub.3).sub.3                                                                            O 2                                         ##STR81##           C(NOH)C.sub.2 H.sub.5                                                                         S 2                                         ##STR82##           CN             O 2                                         ##STR83##           SCN            O 2                                         ##STR84##           NH.sub.2       O 2                                         ##STR85##           N(CH.sub.3).sub.2                                                                             O 2                                         ##STR86##           SCCl.sub.2 F   S 2                                         ##STR87##           SCCl.sub.2 F   O 2                                         ##STR88##           Si(CH.sub.3).sub.3                                                                            O 2                                         ##STR89##           C(NOCH.sub.3)NH.sub.2                                                                         O 2                                         ##STR90##           S(O)OCH.sub.3  O 2                                         ##STR91##           Si(CH.sub.3).sub.3                                                                            O 2                                         ##STR92##                                                                                           ##STR93##     O 2                                         ##STR94##           SO.sub.2 OCH.sub.3                                                                            O 2                                         ##STR95##           SCCl.sub.2 F   O 2                                         ##STR96##           C(NOCH.sub.3)NH.sub.2                                                                         O 2                                         ##STR97##           C(NCH.sub.3)NH.sub.2                                                                          O 2                                         ##STR98##           CN             O 2                                         ##STR99##           SCN            O 2                                        CH.sub.2CHCH.sub.2   SCN            O 2                                        CH.sub.2CHCH.sub.2   SCCl.sub.2 F   O 2                                        CH.sub. 2CHCH.sub.2  SCCl.sub.2 F   O 1                                        CH.sub.2CHCH.sub.2   S(O)OCH.sub.3  O 2                                        CH.sub.2CHCH.sub.2   Si(C.sub.2 H.sub.5).sub.3                                                                     O 2                                        CH.sub.2CHCH.sub.2   NH.sub.2       O 2                                        CH.sub.2CHCH.sub.2   N(CH.sub.3).sub.2                                                                             O 2                                        CH.sub.2CHCH.sub.2   C(NOCH.sub.3)NH.sub.2                                                                         O 2                                        CH.sub.2CHCH.sub.2                                                                                   ##STR100##    O 2                                        CH.sub.2CHCH.sub.2   CN             O 2                                        CH.sub.2CHCH.sub.2   CN             S 2                                        CH.sub.2CCH          CN             O 2                                        CH.sub.2CCH          NH.sub.2       O 2                                        CH.sub.2CCH          N(CH.sub.3).sub.2                                                                             O 2                                        CH.sub.2CCH          SCN            O 2                                        CH.sub.2CCH          SCCl.sub.2 F   O 2                                        CH.sub.2CCH          S(O)OC.sub.2 H.sub.5                                                                          O 2                                        CH.sub.2 CCH                                                                                         ##STR101##    O 2                                        CH.sub.2CCH          C(NOCH.sub.3)NH.sub.2                                                                         O 2                                        CH.sub.2CCH          C(NOH)C.sub.6 H.sub.5                                                                         O 2                                         ##STR102##          CN             O 2                                         ##STR103##          SCN            O 2                                         ##STR104##          C(NOCH.sub.3)NH.sub.2                                                                         O 2                                         ##STR105##          C(NOH)C.sub.6 H.sub.5                                                                         O 2                                         ##STR106##          SCCl.sub.2 F   O 2                                         ##STR107##          S(O)OCH.sub.3  O 2                                         ##STR108##          NH.sub.2       O 2                                         ##STR109##                                                                                          ##STR110##    O 2                                        C(CH.sub.3).sub.2 CHCH.sub.2                                                                        SO.sub.2 OC.sub.2 H.sub.5                                                                     O 2                                        C(CH.sub.3).sub.2 CHCH.sub.2                                                                        CN             O 2                                        C(CH.sub.3).sub.2 CHCH.sub.2                                                                        SCN            O 2                                        C(CH.sub.3).sub.2 CHCH.sub.2                                                                        SCCl.sub.2 F   S 2                                        C(CH.sub.3).sub.2 CHCH.sub.2                                                                        NHCH.sub.3     O 2                                        C(CH.sub.3).sub.2 CHCH.sub.2                                                                        C(NH)N(CH.sub.3).sub.2                                                                        O 2                                        CH(CF.sub.3).sub.2   CN             O 2                                        CH(CF.sub.3).sub.2   SCN            O 2                                        CH(CF.sub.3).sub.2   NH.sub.2       O 2                                        CH(CF.sub.3).sub.2   SCCl.sub.2 F   O 2                                        CH(CF.sub.3).sub.2   S(O)OCH.sub.3  O 2                                        CH(CF.sub.3).sub.2   C(NCH.sub.3)NH.sub.2                                                                          O 2                                        CH(CF.sub.3).sub.2   C(NOCH.sub.3)C.sub.2 H.sub.5                                                                  O 2                                        CH(CF.sub.3).sub.2                                                                                   ##STR111##    O 2                                        CH.sub.2CCCH.sub.2 Cl                                                                               SCN            O 2                                        CH.sub.2CCCH.sub.2 Cl                                                                               NH.sub.2       O 2                                        CH.sub.2CCCH.sub.2 Cl                                                                               SCCl.sub.2 F   O 2                                        CH.sub.2CCCH.sub.2 Cl                                                                               C(NOH)NH.sub.2 O 2                                        CH.sub.2CCCH.sub.2 Cl                                                                               SO.sub.2 OCH.sub.3                                                                            O 2                                        CH.sub.2CCCH.sub.2 Cl                                                                               CN             O 2                                        CH.sub.2CCCH.sub.2 Cl                                                                               CN             S 2                                        CH.sub.2CCCH.sub.2 Cl                                                                               C(NHNH.sub.2)NH.sub.2                                                                         O 2                                        CH.sub.2CCCH.sub.2 Cl                                                                               Si(CH.sub.3).sub.3                                                                            O 2                                        CH.sub.2CHCHCH.sub.2 Cl                                                                             CN             O 2                                        CH.sub.2CHCHCH.sub.2 Cl                                                                             Si(CH.sub.3).sub.3                                                                            O 2                                        CH.sub.2CHCHCH.sub.2 Cl                                                                             S(O)OC.sub.2 H.sub.5                                                                          O 2                                        CH.sub.2 CHCHCH.sub.2 Cl                                                                            SCCl.sub.2 F   O 2                                        CH.sub.2CHCHCH.sub.2 Cl                                                                             NH.sub.2       O 2                                        CH.sub.2CHCHCH.sub.2 Cl                                                                             C(NOCH.sub.3)NHCH.sub.3                                                                       O 2                                        CH.sub.2CHCHCH.sub.2 Cl                                                                             SCN            O 2                                        C(CH.sub.3).sub.2 CCH                                                                               CN             O 2                                        C(CH.sub.3).sub.2 CCH                                                                               SCN            O 2                                        C(CH.sub.3).sub.2 CCH                                                                               C(NOCH.sub.3)NH.sub.2                                                                         O 2                                        C(CH.sub.3).sub.2 CCH                                                                               C(NOH)C.sub.2 H.sub.5                                                                         O 2                                        C(CH.sub.3).sub.2 CCH                                                                               SCCl.sub.2 F   O 2                                        C(CH.sub.3).sub.2 CCH                                                                               SCH.sub.3      O 2                                        C(CH.sub.3).sub.2 CCH                                                                               SO.sub.2 OCH.sub.3                                                                            O 2                                        C(CH.sub.3).sub.2 CCH                                                                                ##STR112##    O 2                                        CH.sub.2 CH.sub.2 OCH.sub.3                                                                         SCCl.sub. 2 F  O 2                                        CH.sub.2 CH.sub.2 OCH.sub.3                                                                         C(NOCOCH.sub.3)NH.sub.2                                                                       O 2                                        CH.sub.2 CH.sub.2 OCH.sub.3                                                                         C(NOH)C.sub.6 H.sub.5                                                                         O 2                                        CH.sub.2 CH.sub.2 OCH.sub.3                                                                         SCN            O 2                                        CH.sub.2 CH.sub.2 OCH.sub.3                                                                         S(O)OC.sub.2 H.sub.5                                                                          O 2                                        CH.sub.2 CH.sub.2 OCH.sub.3                                                                         NH.sub.2       O 2                                        CH.sub.2 CH.sub.2 OCH.sub.3                                                                         NHCH.sub.3     O 2                                        CH.sub.2 CH.sub.2 OCH.sub.3                                                                         CN             S 2                                        CH.sub.2 CH.sub.2 OCH.sub.3                                                                         CN             O 1                                         ##STR113##          CN             O 2                                         ##STR114##          SCN            O 2                                         ##STR115##          SCCl.sub.2 F   O 2                                         ##STR116##          SC.sub.2 H.sub.5                                                                              O 2                                         ##STR117##          S(O)OCH.sub.3  O 2                                         ##STR118##          C(NNH.sub.2)NH.sub.2                                                                          O 2                                         ##STR119##          NH.sub.2       O 2                                        CH.sub.2 CH.sub.2 SCH.sub.3                                                                         SCN            O 2                                        CH.sub.2 CH.sub.2 SCH.sub.3                                                                         CN             O 2                                        CH.sub.2 CH.sub.2 SCH.sub.3                                                                         SC.sub.6 H.sub.4 -p-Cl                                                                        O 2                                        CH.sub.2 CH.sub.2 SCH.sub.3                                                                         SCCl.sub.2 F   O 2                                        CH.sub.2 CH.sub.2 SCH.sub.3                                                                         C(NOCH.sub.3)NH.sub.2                                                                         O 2                                        CH.sub.2 CH.sub.2 SCH.sub.3                                                                         C(NOH)C.sub.2 H.sub.5                                                                         O 2                                        CH.sub.2 CH.sub.2 SCH.sub.3                                                                         N(CH.sub.3).sub.2                                                                             O 2                                        CH.sub.2 CH.sub.2 SCH.sub.3                                                                         NH.sub.2       O 2                                        CH.sub.2 CH.sub.2 SCH.sub.3                                                                         Si(CH.sub.3).sub.3                                                                            O 2                                         ##STR120##          NH-i-C.sub.3 H.sub.7                                                                          O 2                                         ##STR121##          SCCl.sub.2 F   O 1                                         ##STR122##          C(NOCH.sub.3)NH.sub.2                                                                         O 2                                         ##STR123##          CN             O 2                                         ##STR124##          NH.sub.2       O 2                                         ##STR125##          SCN            O 2                                         ##STR126##          C(NH)N(CH.sub.3).sub.2                                                                        O 2                                         ##STR127##                                                                                          ##STR128##    O 2                                         ##STR129##          SCN            S 2                                         ##STR130##          CN             O 2                                         ##STR131##          SCN            O 2                                         ##STR132##          NH.sub.2       O 2                                         ##STR133##          SCCl.sub.2 F   O 2                                         ##STR134##          SCH.sub.3      O 2                                         ##STR135##          C(NOCH.sub.3)NH.sub.2                                                                         O 2                                         ##STR136##          CN             O 2                                         ##STR137##          S(O)OCH.sub.3  O 2                                         ##STR138##                                                                                          ##STR139##    O 2                                         ##STR140##          C(NOCH.sub.3)NH.sub.2                                                                         O 2                                         ##STR141##          C(NH)N(CH.sub.3).sub.2                                                                        O 2                                         ##STR142##          SCCL.sub.2 F   O 2                                         ##STR143##          NH.sub.2       O 2                                         ##STR144##          SCN            S 2                                         ##STR145##          N(CH.sub.3).sub.2                                                                             O 2                                         ##STR146##          SCCl.sub.2 F   O 2                                         ##STR147##          SCH.sub.3      O 2                                         ##STR148##          NH.sub.2       O 2                                         ##STR149##                                                                                          ##STR150##    O 2                                         ##STR151##          SCN            O 2                                         ##STR152##          CN             O 2                                        CH.sub.2 CO.sub.2 CH.sub.3                                                                          N(C.sub.2 H.sub.5).sub.2                                                                      O 2                                        CH.sub.2 CO.sub.2 CH.sub.3                                                                           ##STR153##    O 2                                        CH.sub.2 CO.sub.2 CH.sub.3                                                                          CN             O 2                                        CH.sub.2 CO.sub.2 CH.sub.3                                                                          SCN            O 2                                        CH.sub.2 CO.sub.2 CH.sub.3                                                                          NH.sub.2       O 1                                        CH.sub.2 CO.sub.2 CH.sub.3                                                                          SC.sub.6 H.sub.4 -p-Cl                                                                        O 2                                        CH.sub.2 CO.sub.2 CH.sub.3                                                                          C(NOC.sub.2 H.sub.5)NH.sub.2                                                                  O 2                                        CH.sub.2 CO.sub.2 CH.sub.3                                                                           ##STR154##    O 2                                         ##STR155##          CN             O 2                                         ##STR156##          CN             O 1                                         ##STR157##          SCN            O 2                                         ##STR158##          C(NOCH.sub.3)NH.sub.2                                                                         O 2                                         ##STR159##          C(NOCH.sub.3)C.sub.2 H.sub.5                                                                  O 2                                         ##STR160##          SCCl.sub.2 F   O 2                                         ##STR161##          S(O)OCH.sub.3  O 2                                         ##STR162##                                                                                          ##STR163##    O 2                                         ##STR164##          NH.sub.2       O 2                                         ##STR165##          SCCl.sub.2 F   O 2                                         ##STR166##          C(NOH)NH.sub.2 O 2                                         ##STR167##          C(NH)N(CH.sub.3).sub.2                                                                        O 2                                         ##STR168##          N(CH.sub.3).sub.2                                                                             O 2                                         ##STR169##                                                                                          ##STR170##    O 2                                         ##STR171##          CN             O 2                                         ##STR172##          SCN            O 2                                         ##STR173##          CN             O 2                                         ##STR174##          SCCl.sub.2 F   O 2                                         ##STR175##          SCH.sub.3      O 2                                         ##STR176##          S(O)OCH.sub.3  S 2                                         ##STR177##          NH-i-C.sub.3 H.sub.7                                                                          O 2                                         ##STR178##          NH.sub.2       O 2                                         ##STR179##          C(NOH)NH.sub.2 O 2                                         ##STR180##          Si(CH.sub.3).sub.3                                                                            O 2                                         ##STR181##          CN             O 2 174-175                                 ##STR182##          SCN            O 2                                         ##STR183##          SCCl.sub.2 F   O 2                                         ##STR184##          NH.sub.2       O 2                                         ##STR185##          C(NOH)NH.sub.2 O 2                                         ##STR186##          SO.sub.2 OCH.sub.3                                                                            O 2                                         ##STR187##          Si(CH.sub.3).sub.3                                                                            O 2                                         ##STR188##          CN             S 2                                         ##STR189##          CN             O 2                                         ##STR190##          SCN            O 2                                         ##STR191##          NH.sub.2       O 2                                         ##STR192##          SCCl.sub.2 F   O 2                                         ##STR193##          S(O)OCH.sub.3  O 2                                         ##STR194##          CN             O 2                                         ##STR195##          SCN            O 2                                         ##STR196##          SCH.sub.3      O 2                                         ##STR197##          SO.sub.2 OCH.sub.3                                                                            O 2                                         ##STR198##          N(CH.sub.3).sub.2                                                                             O 2                                         ##STR199##          NH.sub.2       O 1                                         ##STR200##          CN             O 2                                         ##STR201##          NH.sub.2       O 2                                         ##STR202##          SCN            O 2                                         ##STR203##          C(NOCH.sub.3)C.sub.2 H.sub.5                                                                  O 2                                         ##STR204##          CN             O 2                                         ##STR205##          CN             S 2                                         ##STR206##          CN             O 2                                         ##STR207##          CN             O 2                                        __________________________________________________________________________

                                      table 2                                      __________________________________________________________________________            ring                                                                    X      position                                                                            m R.sup.1   R.sup.2 Y n m.p.(°C.)                           __________________________________________________________________________     CH.sub.3                                                                              5,6,7                                                                               1 CH.sub.3  CN      O 2                                            CH.sub.3                                                                              5,6,7,8                                                                             1 C.sub.2 H.sub.5                                                                          CN      O 2                                            CH.sub.3                                                                              5,6,7,8                                                                             1 n-C.sub.3 H.sub.7                                                                        CN      O 2                                            CH.sub.3                                                                              8    1 i-C.sub.3 H.sub.7                                                                        CN      O 2 103-104                                    CH.sub.3                                                                              8    1 i-C.sub.3 H.sub.7                                                                        SCN     O 2                                            CH.sub.3                                                                              8    1 i-C.sub.3 H.sub.7                                                                        NH.sub.2                                                                               O 2                                            CH.sub.3                                                                              8    1 i-C.sub.3 H.sub.7                                                                        C(NOH)NH.sub.2                                                                         O 2                                            CH.sub.3                                                                              8    1 i-C.sub.3 H.sub.7                                                                        SCCl.sub.2 F                                                                           O 2                                            CH.sub.3                                                                              8    1 i-C.sub.3 H.sub.7                                                                        S(O)OCH.sub.3                                                                          O 2                                            CH.sub.3                                                                              8    1 i-C.sub.3 H.sub.7                                                                        Si(CH.sub.3).sub.3                                                                     O 2                                            CH.sub.3                                                                              6,8  2 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            Br     6    1 i-C.sub.3 H.sub.7                                                                        CN      O 2 76-77                                      Br     5,7,8                                                                               1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            Br     6,8  2 i-C.sub.3 H.sub.7                                                                        CN      O 2 119-120                                    Br     6    1 sec C.sub.4 H.sub.9                                                                      CN      O 2                                            Br     6    1 sec C.sub.4 H.sub.9                                                                      CN      S 2                                            Cl     5,6  1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            Cl     7    1 i-C.sub.3 H.sub.7                                                                        CN      O 2 146-147                                    Cl     7    1 i-C.sub.3 H.sub.7                                                                        NH.sub.2                                                                               O 2                                            Cl     7    1 i-C.sub.3 H.sub.7                                                                        SCN     O 2                                            Cl     7    1 i-C.sub.3 H.sub.7                                                                        SCCl.sub.2 F                                                                           O 2                                            Cl     7    1 i-C.sub.3 H.sub.7                                                                        N(CH.sub.3).sub.2                                                                      O 2                                            Cl     7    1 sec C.sub.4 H.sub.9                                                                      CN      O 2                                            Cl     8    1 i-C.sub.3 H.sub.7                                                                        CN      O 2 123-124                                    Cl     8    1 i-C.sub.3 H.sub.7                                                                        SCN     O 2                                            Cl     8    1 i-C.sub.3 H.sub.7                                                                        NH.sub.2                                                                               O 2                                            Cl     8    1 i-C.sub.3 H.sub.7                                                                        n(CH.sub.3).sub.2                                                                      O 2                                            Cl     8    1 i-C.sub.3 H.sub.7                                                                        SCH.sub.3                                                                              O 2                                            Cl     8    1 i-C.sub.3 H.sub.7                                                                        SCCl.sub.2 F                                                                           S 2                                            Cl     8    1 i-C.sub.3 H.sub.7                                                                        S(O)OCH.sub.3                                                                          O 2                                            Cl     8    1 i-C.sub.3 H.sub.7                                                                        Si(CH.sub.3).sub.3                                                                     O 2                                            Cl     5,6,7,8                                                                             1 n-C.sub.3 H.sub.7                                                                        CN      O 2                                            F      5,6,7                                                                               1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            F      5,6,7,8                                                                             4 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            CH.sub.3                                                                              6                                                                                   2 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            Cl     8                                                                        ##STR208##                                                                           8    1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                             ##STR209##                                                                           5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            ClCH.sub.2                                                                            5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            NO.sub.2                                                                              5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            NO.sub.2                                                                              5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 1                                            F      8    1 i-C.sub.3 H.sub.7                                                                        CN      O 2 89-91                                      NO.sub.2                                                                              5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            NO.sub.2                                                                              6,8  2 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            CH.sub.3                                                                              6,8  2 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            NO.sub.2                                                                       NH.sub.2                                                                              5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            CH.sub.3                                                                              6,8  2 sec C.sub.4 H.sub.9                                                                      CN      O 2                                            NO.sub.2                                                                       SCN    5,6,7,8                                                                             1 C.sub.2 H.sub.5                                                                          CN      O 2                                            SCN    5,6,7,8                                                                             1 n-C.sub.3 H.sub. 7                                                                       CN      O 2                                            SCN    5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            SCN    5,6,7,8                                                                             1                                                                                 ##STR210##                                                                              CN      O 2                                            CO.sub.2 CH.sub.3                                                                     5,6,8                                                                               1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            CO.sub.2 CH.sub.3                                                                     7    1 i-C.sub.3 H.sub.7                                                                        CN      O 2 126-127                                    CO.sub.2 CH.sub.3                                                                     5,6,7,8                                                                             1 sec C.sub.4 H.sub.9                                                                      CN      O 2                                            CO.sub.2 CH.sub.3                                                                     5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      S 2                                            N(CH.sub.3).sub.2                                                                     5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            N(CH.sub.3).sub.2                                                                     5,6,7,8                                                                             1 n-C.sub.3 H.sub.7                                                                        CN      O 2                                            OCH.sub.3                                                                             5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            OCH.sub.3                                                                             5,6,7,8                                                                             1 sec C.sub.4 H.sub.9                                                                      SCN     O 2                                            OCH.sub.3                                                                             5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        N(CH.sub.3).sub.2                                                                      O 2                                            SCH.sub.3                                                                             5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            SCH.sub.3                                                                             5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        SCN     O 2                                            SO.sub.2 CH.sub.3                                                                     5,6,7,8                                                                             1 CH.sub.3  CN      O 2                                            SO.sub.2 CH.sub.3                                                                     5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            SO.sub.2 CH.sub.3                                                                     5,6,7,8                                                                             1 sec C.sub.4 H.sub.9                                                                      CN      O 2                                            SO.sub.2 OCH.sub.3                                                                    5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            SO.sub.2 OCH.sub.3                                                                    5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        N(CH.sub.3).sub.2                                                                      O 2                                            SO.sub.2 OCH.sub.3                                                                    5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        NH.sub.2                                                                               O 1                                            SO.sub.2 OCH.sub.3                                                                    5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            SO.sub.2 N(CH.sub.3).sub.2                                                            5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        SCN     O 2                                            CCl.sub.3                                                                             5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            CCl.sub.3                                                                             5,6,7,8                                                                             1 sec C.sub.4 H.sub.9                                                                      CN      O 2                                            CF.sub.3                                                                              5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            CF.sub.3                                                                              5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        SCN     O 2                                            CF.sub.3                                                                              5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        N(CH.sub.3).sub.2                                                                      O 2                                             ##STR211##                                                                           5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                             ##STR212##                                                                           5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            OH     5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            SH     5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            SO.sub.2 NHCH.sub.3                                                                   5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            SO.sub. 2 NHC.sub.2 H.sub.5                                                           5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        SCN     O 2                                            OCF.sub.2 CF.sub.3                                                                    5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            OCF.sub.2 CF.sub.3                                                                    5,6,7,8                                                                             1 sec C.sub.4 H.sub.9                                                                      CN      O 2                                            OCF.sub.2 CH.sub.3                                                                    5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            OCF.sub.2 CCl.sub.3                                                                   5,6,7,8                                                                             1 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            Cl     5,6,7,8                                                                             1 C.sub.6 H.sub.5                                                                          CN      O 2                                            Cl     5,6,7,8                                                                             1                                                                                 ##STR213##                                                                              CN      O 2                                            Cl     5,6,7,8                                                                             1                                                                                 ##STR214##                                                                              CN      O 2                                            Cl     5,6,7,8                                                                             1                                                                                 ##STR215##                                                                              CN      O 2                                            Cl     5,6,7,8                                                                             1                                                                                 ##STR216##                                                                              CN      S 2                                            CH.sub.3                                                                              5,6,7,8                                                                             1 C.sub.6 H.sub.5                                                                          CN      O 2                                            CH.sub.3                                                                              5,6,7,8                                                                             1                                                                                 ##STR217##                                                                              CN      O 2                                            CH.sub.3                                                                              5,6,7,8                                                                             1                                                                                 ##STR218##                                                                              CN      O 2                                            Cl     5,6,7,8                                                                             1                                                                                 ##STR219##                                                                              CN      O 2                                            CH.sub.3                                                                              5,6,7,8                                                                             1 CH.sub.2 CHCH.sub.2                                                                      CN      O 2                                            CH.sub.3                                                                              5,6,7,8                                                                             1 C(CH.sub.3 ).sub.3                                                                       CN      O 2                                            Cl     5,6,7,8                                                                             1 CH.sub.2 CHCH.sub.2                                                                      CN      O 2                                            CH.sub.3                                                                              5,6,7,8                                                                             1                                                                                 ##STR220##                                                                              CN      O 2                                            CH.sub.3                                                                              5,6,7,8                                                                             1                                                                                 ##STR221##                                                                              SCN     O 2                                            Cl     5,6,7,8                                                                             1                                                                                 ##STR222##                                                                              CN      O 2                                            CH.sub.3                                                                              5,6,7,8                                                                             1                                                                                 ##STR223##                                                                              CN      O 2                                            Cl     5,6,7,8                                                                             1                                                                                 ##STR224##                                                                              CN      O 2                                            CH.sub.3                                                                              5,6,7,8                                                                             1                                                                                 ##STR225##                                                                              CN      O 2                                            CH.sub.3                                                                              5,6,7,8                                                                             1                                                                                 ##STR226##                                                                              CN      O 2                                            CH.sub.3                                                                              5,6,7,8                                                                             1                                                                                 ##STR227##                                                                              CN      S 2                                            CH.sub.3                                                                              5,6,7,8                                                                             1                                                                                 ##STR228##                                                                              CN      O 1                                            Br(6), CH.sub.3 (8)                                                                   6,8  2 i-C.sub.3 H.sub.7                                                                        CN      O 2                                            __________________________________________________________________________

experiments for determining the herbicidal action of the new 2,1,3-benzothiadiazine compounds

The herbicidal and selective properties of the new compounds were investigated in greenhouse and field experiments.

EXAMPLE 7 (greenhouse experiments)

Plastic flowerpots having a volume of 300 cm³ were filled with a sandy loam. Seeds were then sown, pregerminated tubers (e.g. Cyperus esculentus) planted or vegetatively reproduced species transplanted. The test plants were separated according to species. Only seeds were used for the preemergence treatment. The active ingredients were suspended or emulsified in water as the vehicle and sprayed onto the surface of the soil by means of atomizing nozzles. After treatment, the vessels were lightly sprinkler-irrigated and then covered with transparent plastic hoods until the plants had taken root. For the postemergence (leaf) treatment, the plants were first grown to a height of from 3 to 10 cm, depending on habit, before being treated. The pots were of course not irrigated, and no hoods were placed on the pots. The plants were placed in either cooler or warmer parts of the greenhouse, depending on their temperature requirements. The experiments were run for from 2 to 4 weeks. During this period the plants were tended and their reaction to the individual treatments was assessed. The application rate of the compounds examined is given in kg/ha of active ingredient. For assessment, the 0 to 100 scale was used, 0 denoting no damage or normal emergence, and 100 denoting no emergence or complete destruction.

EXAMPLE 8 (experiments in the open)

Postemergence treatments were carried out on small plots. The compounds were applied, as an emulsion or suspension in water, with the aid of a motor-driven plot spray mounted on a hitch. All the experiments were observed for several weeks and again assessed on the 0 to 100 scale.

Results

The following statements may be made with regard to the new compounds:

1. The action of the compounds when applied to the soil (preemergence) was approximately equivalent to that of the comparative agent. A shift in action was indicated (Table 2).

2. The introduction of the cyano group in the 1-position in the 2,1,3-benzothiadiazin-(4)-one-2,2-dioxides resulted in a surprising increase in action and in an extension of the spectrum of combattable unwanted plant species (Tables 3, 4, 5, 6, 7 and 8). An additional feature is the increased reliability of the new compounds.

3. The new compounds are well tolerated by numerous crop plants (Tables 3, 4, 5, 6, 7 and 8).

The compounds according to the invention are therefore of outstanding value as selective herbicides, and represent a considerable enrichment of the art.

                  Table 1                                                          ______________________________________                                         List of plant names                                                                        Abbreviation in                                                    Botanical name                                                                             tables      Common name                                            ______________________________________                                         Abutilon theophrastii                                                                      Abut. theo. velvet leaf                                            Anthemis spp.                                                                              Anth.       chamomile                                              Arachys hypogaea                                                                           Arachys hyp.                                                                               peanuts (groundnuts)                                   Bidens pilosa                                                                              Bidens pil.                                                        Chenopodium album                                                                          Chen. alb.  lambsquarters                                          Cyperus difformis                                                                          Cyp. diff.  smallflower umbrellaplant                              Cyperus esculentus                                                                         Cyper. escul.                                                                              yellow nutsedge                                        Cyperus ferax                                                                              Cyper. ferox                                                       Daucus carota                                                                                --        carrot                                                 Galinsoga spp.                                                                             Galins. spp.                                                                               gallant soldier                                        Galium aparine                                                                             Galium apar.                                                                               catchweed bedstraw                                     Glycine max Glyc. max   soybeans                                               Lamium spp. Lam. spp.   dead-nettle (henbit)                                   Ludwigia prostrata                                                                         Ludw. pros.                                                        Matricaria spp.                                                                            Matric. spp.                                                                               chamomile                                              Medicago sativa                                                                            Medi. sat.  alfalfa                                                Mercurialis annua                                                                          Mercur. annua                                                                              annual mercury                                         Oryza sativa                                                                               Oryza sat.  rice                                                   Phaseolus vulgaris                                                                         Phaseo. vulg.                                                                              snapbean                                               Portulaca oleracea                                                                         Port. oler. common purslane                                        Sesbania exaltata                                                                          Sesb. exal. hemp sesbania                                                                  (coffeeweed)                                           Sida spinosa                                                                               Sida spin.  teaweed (prickly sida)                                 Sinapis alba                                                                                 --        white mustard                                          Sinapis arvensis                                                                            Sinap. arv.                                                                               yellow charlock                                        Sorghum bicolor                                                                            Sorgh. bic. sorghum                                                Solanum nigrum                                                                             Sol. nig.   black nightshade                                       Stellaria media                                                                            Stellaria media                                                                            chickweed                                              Triticum aestivum                                                                          Triti. aest.                                                                               wheat                                                  Zea mays      --        Indian corn                                            Centaurea cyanus                                                                             --        cornflower                                             ______________________________________                                    

                                      Table 2                                      __________________________________________________________________________     Preemergence application in the greenhouse                                      ##STR229##                                                                    Compound                                                                             Substituents                                                                         Appl. rate                                                                           Test plants and % damage                                     no.   R     ka/ha Daucus carota                                                                          Sida spinosa                                                                          Sinapis alba                                  __________________________________________________________________________     1     CN    1.0    90     55     80                                                        2.0    90     78     80                                            2 prior art                                                                          H     1.0   100     70     40                                            (German     2.0   100     90     80                                            1 542 836)                                                                     __________________________________________________________________________      0 = no damage                                                                  100 = complete destruction                                               

                                      Table 3                                      __________________________________________________________________________     Areas of action and application; postemergenece treatment in the               greenhouse                                                                     Appl.     Test plants and % damage                                             Compound                                                                             rate                                                                               Glyc.                                                                              Medi.                                                                              Phaseo.                                                                             Sorgh.                                                                             Abut.                                                                              Cyp.                                                                              Chen.                                                                              Lamium                                                                              Merc.                                                                              Port.                                                                             Sesb.                                                                              Stell.                   no.   kg/ha                                                                              max sat.                                                                               vulg.                                                                               bic.                                                                               thoe.                                                                              diff.                                                                             alb.                                                                               spp. ann.                                                                               oler.                                                                             exalt.                                                                             med.                     __________________________________________________________________________     1     1,0 0   0    0   0   99  47 50  100  100 100                                                                               60  100                            2,0 0   0   10   0   99  60 85  100  100 100                                                                               80  100                            4,0 3   0   10   0   --  68 --  --   --  -- --  --                       2     1,0 0   0   0    0   99  53 65  50   30  100                                                                               50  95                             2,0 0   0   0    0   99  67 65  50   60  100                                                                               60  95                             4,0 0   20  0    0   --  70 --  --   --  -- --  --                       __________________________________________________________________________      0 = no damage                                                                  100 = complete destruction                                               

                                      Table 4                                      __________________________________________________________________________     Removal of unwanted plants from soybeans and Indian corn;                      postemergence treatment in the open                                            Appl.     Test plants and % damage                                             Compound                                                                             rate                                                                               Glycine max     Zea                                                                                Anth./                                                                            Galins.                                                                            Lamium                                                                              Stell.                                                                            Sinap.                            no.   kg/ha                                                                              cv. Bragg                                                                           cv. Dare                                                                            cv. SRF 450                                                                          mays                                                                               Matr.                                                                              spp.                                                                               spp.                                                                               med.                                                                              arv.                              __________________________________________________________________________     1.    0,5 0    2 kg/ha                                                                             0     0  80  82  45   91 100                                     1,0 0    0    2     0  96  96  70   99 100                                     4,0   2,5     11    -- 100 100 100  100                                                                               100                               2.    0,5 0    --   0     0   94 71  17   92 100                                     1,0 0    12   4     0  100 88  53   98 100                                     4,0 17   --   14    -- 100 100 100  100                                                                               100                               __________________________________________________________________________      0 = no damage                                                                  100 = complete destruction                                               

                                      Table 5                                      __________________________________________________________________________     Herbicidal action after postemergence application in the greenhouse             ##STR230##                                                                                 Appl.                                                                              Test plants and % damage                                      Substituents rate                                                                               Tritic.                                                                            Chenop.                                                                             Cyper.                                                                             Matr.                                                                              Merc.                                                                              Sinapis                                                                            Stell.                               R.sup.1   R.sup.2                                                                           kg/ha                                                                               aest.                                                                             album                                                                               escul.                                                                              spp.                                                                              annua                                                                              arv.                                                                               med.                                 __________________________________________________________________________     CH.sub.3  CH.sub.3                                                                          2.0 0   0    0   0   0   0   0                                    prior art                                                                      (German Laid-Open                                                              Application                                                                    DOS 2,443,901)                                                                 CN        CH.sub.3                                                                          1.0 0   100  0   100 100 100 100                                  CN        Cl 1.0 0   100  65  100 100 100 100                                  __________________________________________________________________________      0 = no damage                                                                  100 = complete destruction                                               

                                      Table 6                                      __________________________________________________________________________     Herbicidal action after postemergence application in the greenhouse             ##STR231##                                                                                    Test plants and % damage                                       Substituents    Glyc.                                                                              Triti.                                                                             Zea Cyper.                                                                             Galium                                                                              Lam.                                                                              Ludw.                                                                              Sida                                                                              Sesb.                                                                              Sol.                        R.sub.1   R.sub.2                                                                          kg/ha                                                                               max                                                                               aest.                                                                              mays                                                                               esc.                                                                               apar.                                                                               spp.                                                                              pros.                                                                              spin.                                                                             exal.                                                                              nig.                        __________________________________________________________________________     CN        Cl                                                                               0.25                                                                               --  --  0   --  50   -- 78  86 100 100                                     1.0 0   3   0   68  78   73 95  100                                                                               100 100                                     2.0 6   7   5   78  95   72 --  100                                                                               100 100                         H         Cl                                                                               0.25                                                                               --  --  --  --  36   -- 65  55  90  86                         prior art   1.0 0   2   0   36  63   20 95  98 100 100                         (German Laid-Open                                                                        2.0                                                                              0   2   0   41  71  30   -- 98  100                                                                               100                             Application                                                                    DOS 2,443,901)                                                                 __________________________________________________________________________      O = no damage                                                                  100 = complete destruction                                               

                                      Table 7                                      __________________________________________________________________________     Herbicidal action of the new compounds                                          ##STR232##                                                                               Test plants and % damage                                            Substituents                                                                              Arachys                                                                             Glyc.                                                                              Oryza                                                                              Triti.                                                                             Abut.                                                                              Bidens                                                                             Cyper.                                                                             Mercur.                                                                             Sol.                              R.sub.1                                                                             R.sub.2                                                                          kg/ha                                                                               hyp.                                                                               max sat.                                                                               aest.                                                                              theo.                                                                              pil.                                                                               ferax                                                                              annua                                                                               nig.                              __________________________________________________________________________     CN   F 0.25                                                                               --   0   --  0   100 100 95  99   100                                      1.0 10   0   15  0   100 100 100 99   100                               H    H 0.25                                                                               --   0   --  2    69  63 50  42    93                               prior art                                                                             1.0  0   0    5  2    87  90 80  65   100                               __________________________________________________________________________      0 = no damage                                                                  100 = complete destruction                                               

                  Table 8                                                          ______________________________________                                         Herbicidal action of the new compounds; postemergence                          application in the open                                                         ##STR233##                                                                                 Test plants and % damage                                          Substituents       Triti.  Galium Matric.                                                                              Stellaria                              R.sub.1 R.sub.2                                                                               kg/ha   aest. apar.   spp. media                                ______________________________________                                         CN      H      0.5     0     45     100   95                                                  1.0     0     68     100   98                                                  1.5     0     95     100   100                                  CN      CH.sub.3                                                                              0.5     0     65     100   95                                                  1.0     0     85     100   100                                                 1.5     0     92     100   100                                  H       H      0.5     0     10     100   65                                   prior art      1.0     0     30     100   85                                   (German        1.5     0     70     100   98                                   1,542,836)                                                                     H       CH.sub.3                                                                              0.5     0     12      95   45                                   prior art      1.0     0     30     100   65                                   (German        1.5     0     50     100   75                                   2,443,901)                                                                     ______________________________________                                          0 = no damage                                                                  100 = complete destruction                                               

                                      Table 9                                      __________________________________________________________________________     Herbicidal action of the new compounds in Sinapis alba and Centaurea           cyanus;                                                                        postemergence application in the greenhouse                                     ##STR234##                                                                    Substituents        Ring       Sinapis alba                                    R.sub.1   R.sub.2                                                                             X    substitution                                                                          kg/ha                                                                              % damage                                        __________________________________________________________________________     CN        CH.sub.3                                                                            H    --     2,0 100                                             CN        C.sub.2 H.sub.5                                                                     H    --     2,0 100                                             CN        C.sub.4 H.sub.9 sec                                                                 H    --     2,0  85                                             CN                                                                                        ##STR235##                                                                         H    --     2,0  90                                             CN        C.sub.3 H.sub.7 i                                                                   Cl   7      2,0 100                                             CN        C.sub.3 H.sub.7 i                                                                   Br.sub.2                                                                            6,8    2,0  80                                              ##STR236##                                                                              C.sub.3 H.sub.7 i                                                                   H    --     2,0 100                                              ##STR237##                                                                              C.sub.3 H.sub.7 i                                                                   H    --     2,0 100                                                                            Centaurea cyanus                                SCCl.sub.2 F                                                                             C.sub.2 H.sub.5                                                                     H    --     2,0 100                                             CN        C.sub.3 H.sub.7 i                                                                   Br.sub.2 CH.sub.3                                                                   6,8    3,0 100                                             __________________________________________________________________________      0 = no damage                                                                  100 = complete destruction                                               

Suitable application methods for the new active ingredients are soil incorporation, treatment of the soil surface, and particularly postemergence treatment. Special applications such as post-directed or lay-by treatment are also possible. In this case, the spray is directed in such a manner that the leaves of sensitive crop plants are not touched; the agents are sprayed onto the soil beneath the crop plants, or the unwanted plants growing there.

In view of the wide variety of application methods, the agents according to the invention, or compositions containing them, may be used not only in the crop plants in the above tables, but also in a further large number of crop plants for eliminating unwanted plants. The application rates may vary from 0.1 to 15 kg/ha and more.

The following crop plants may be mentioned by way of example:

    ______________________________________                                         Botanical Name     Common name                                                 ______________________________________                                         Allium cepa        onion                                                       Ananas comosus     pineapple                                                   Asparagus officinalis                                                                             asparagus                                                   Avena sativa       oats                                                        Beta vulgaris spp. altissima                                                                      sugarbeet                                                   Beta vulgaris spp. rapa                                                                           fodder beet                                                 Beta vulgaris spp. esculenta                                                                      table beet, red beet                                        Brassica napus var. napus                                                                         rape                                                        Brassica napus var. napobrassica                                               Brassica napus va. rapa                                                                           turnip                                                      Brassica rapa var. silvestris                                                  Camellia sinensis  tea plant                                                   Carthamus tinctorius                                                                              safflower                                                   Citrus limon       lemon                                                       Citrus maxima      grapefruit                                                  Citrus reticulata                                                              Citrus sinensis    orange                                                      Coffea arabica (Coffea canaphora,                                              Coffea liberica)   coffee                                                      Cucumis melo       melon                                                       Cucumis sativus    cucumber                                                    Cynodon dactylon   Bermudagrass in turf and                                                       lawns                                                       Elaeis guineensis  oil palm                                                    Fragaria vesca     strawberry                                                  Gossypium hirsutum                                                             (Gossypium arboreum                                                            Gossypium herbaceum                                                                               cotton                                                      Gossypium vitifolium)                                                          Helianthus annuus  sunflower                                                   Helianthus tuberosus                                                           Hevea brasiliensis rubber plant                                                Hordeum vulgare    barley                                                      Humulus lupulus    hops                                                        Ipomoea batatas    sweet potato                                                Lactuca sativa     lettuce                                                     Lens culinaris     lentil                                                      Linum usitatissimum                                                                               flax                                                        Lycopersicon lycopersicum                                                                         tomato                                                      Malusspp.          apple                                                       Manihot esculenta  cassava                                                     Mentha piperita    peppermint                                                  Musaspp.           banana                                                      Nicotiana tabacum  tobacco                                                     (N. rustica)                                                                   Olea europaea      olive                                                       Panicum miliaceum                                                              Phaseolus lunatus  limabean                                                    Phaseolus mungo    mungbean                                                    Pennisetum glaucum                                                             Petroselinum crispum                                                                              parsley                                                     spp.tuberosum                                                                  Picea abies        Norway spruce                                               Abies alba         fir                                                         Pinus spp.         pine                                                        Pisum sativum      English pea                                                 Prunus avium       cherry                                                      Prunus domestica   plum                                                        Prunus persica     peach                                                       Pyrus communis     pear                                                        Ribes sylvestre    red currant                                                 Ribes uva-crispa                                                               Ricinus communis                                                               Saccharum officinarum                                                                             sugar cane                                                  Secale cereale     rye                                                         Sesamum indicum    Sesame                                                      Solanum tuberosum  Irish potato                                                Sorghum dochna                                                                 Spinacia oleracea  spinach                                                     Theobroma cacao    cacao                                                       Trifolium pratense red clover                                                  Vaccinium corymbosum                                                                              blueberry                                                   Vaccinium vitis-idaea                                                                             cranberry                                                   Vicia faba         tick bean                                                   Vigna sinensis (V. unguiculata)                                                                   cow pea                                                     Vitis vinifera     grape                                                       ______________________________________                                    

To extend the spectrum of action of the new individual active ingredients, to achieve synergistic effects or to improve persistence in the soil, numerous other herbicidal and growth-regulating compounds may be used as components in compositions and combinations. Depending on the intended area of use and the envisaged objective, the following compounds or similar derivatives may be used:

    __________________________________________________________________________             ##STR238##                                                                                            ##STR239##                                              ##STR240##            and salts                                         ##STR241##                                                                           R             R.sub.1      R.sub.2                                      __________________________________________________________________________             ##STR242##   NH.sub.2     Cl                                                   ##STR243##   NHCH.sub.3   Cl                                            ##STR244##                                                                     R     R.sub.1   R.sub.2                                                                               R.sub.3   R.sub.4                                      __________________________________________________________________________     H      SO.sub.2 NH.sub.2                                                                        H      n-C.sub.3 H.sub.7                                                                        n-C.sub.3 H.sub.7                            H.sub.3 C                                                                             H.sub.3 C H      H                                                                                         ##STR245##                                   ##STR246##                                                                    R                  R.sub.1 R.sub.2                                             __________________________________________________________________________      ##STR247##        H                                                                                       ##STR248##                                          ##STR249##        H       CH.sub.2CCCH.sub.2 Cl                                ##STR250##        H       i-C.sub.3 H.sub.7                                    ##STR251##        H       CH.sub.3                                             ##STR252##                                                                    R                  R.sub.1 R.sub.2                                             __________________________________________________________________________      ##STR253##        H       CH.sub.3                                             ##STR254##        H       C.sub.2 H.sub.5                                      ##STR255##        CH.sub.3                                                                               CH.sub.3                                             ##STR256##        H       CH.sub.3                                             ##STR257##                                                                     ##STR258##                                                                     ##STR259##                                                                    R                       X   Y   R.sub.1                                        __________________________________________________________________________     CH.sub.3                Cl  Cl  Na                                              ##STR260##             Cl  H   CH.sub.3                                        ##STR261##             H   H   H salts                                         ##STR262##             H   CH.sub.3                                                                           CH.sub.3                                        ##STR263##             H   CH.sub.3                                                                           C.sub.2 H.sub.5                                 ##STR264##             H   CH.sub.3                                                                           i-C.sub.3 H.sub.7                               ##STR265##             H   CH.sub.3                                                                           CH.sub.3                                        ##STR266##             H   CH.sub.3                                                                            ##STR267##                                     ##STR268##             H   CH.sub.3                                                                           Na                                              ##STR269##             H   CH.sub.3                                                                           Na                                              ##STR270##                                                                    R    R.sub.1    X      R.sub.2                                                                              R.sub.3                                           __________________________________________________________________________     H    tert.-C.sub.4 H.sub.9                                                                     SCH.sub.3                                                                             H     C.sub.2 H.sub.5                                   H    i-C.sub.3 H.sub.7                                                                         SCH.sub.3                                                                             H     i-C.sub.3 H.sub.7                                 H    C.sub.2 H.sub.5                                                                           SCH.sub.3                                                                             H     C.sub.2 H.sub.5                                   H    i-C.sub.3 H.sub.7                                                                         SCH.sub.3                                                                             H     C.sub.2 H.sub.5                                   H    i-C.sub.3 H.sub.7                                                                         Cl     H     C.sub.2 H.sub.5                                   H    i-C.sub.3 H.sub.7                                                                         Cl     H                                                                                     ##STR271##                                       H    C.sub.2 H.sub.5                                                                           Cl     H     C.sub.2 H.sub.5                                   H    C.sub.2 H.sub.5                                                                           Cl     H                                                                                     ##STR272##                                       H    i-C.sub.3 H.sub.7                                                                         Cl     H     i-C.sub.3 H.sub.7                                 H    i-C.sub.3 H.sub.7                                                                         OCH.sub.3                                                                             H     iC.sub.3 H.sub.7                                  H    C.sub.2 H.sub.5                                                                           Cl     H                                                                                     ##STR273##                                       H    C.sub.2 H.sub.5                                                                           Cl     H                                                                                     ##STR274##                                             ##STR275##                                                                               Cl     H                                                                                     ##STR276##                                        ##STR277##                                                                    R                    R.sub.1                                                                              R.sub.2                                             __________________________________________________________________________      ##STR278##          H                                                                                     ##STR279##                                          ##STR280##          H     C.sub.2 H.sub.5                                      ##STR281##          H                                                                                     ##STR282##                                          ##STR283##          H                                                                                     ##STR284##                                          ##STR285##          H     CH.sub.3                                             ##STR286##                                                                             X          Y          R                                               __________________________________________________________________________              Br         Br         H salts                                                  I          I          H salts                                          ##STR287##                       salts, esters                                 ##STR288##                       salts, esters                                 ##STR289##                                                                    R                     R.sub.1                                                                             R.sub.2                                                                             R.sub.3                                        __________________________________________________________________________      ##STR290##           H    CH.sub.3                                                                            CH.sub.3                                        ##STR291##           H    CH.sub.3                                                                            CH.sub.3                                        ##STR292##           CH.sub.3                                                                            CH.sub.3                                                                            H                                               ##STR293##           H    CH.sub.3                                                                            CH.sub.3                                        ##STR294##           H    CH.sub.3                                                                            CH.sub.3                                        ##STR295##           H    CH.sub.3                                                                             ##STR296##                                     ##STR297##           H    CH.sub.3                                                                            OCH.sub.3                                       ##STR298##           H    CH.sub.3                                                                            OCH.sub.3                                       ##STR299##           H    CH.sub.3                                                                            CH.sub.3                                        ##STR300##           H    CH.sub.3                                                                            OCH.sub.3                                       ##STR301##           H    CH.sub.3                                                                            OCH.sub.3                                       ##STR302##           H    CH.sub.3                                                                            CH.sub.3                                        ##STR303##           CH.sub.3                                                                            CH.sub.3                                                                            H                                               ##STR304##                                                                     ##STR305##           H    CH.sub.3                                                                            OCH.sub.3                                       ##STR306##           H    CH.sub.3                                                                            CH.sub.3                                        ##STR307##                                                                    R             R.sub.1 R.sub.2  R.sub.3                                         __________________________________________________________________________     Cl            Cl      Cl       H                                               F             Cl      Cl       H                                               NO.sub.2      CF.sub.3                                                                               H        H                                               Cl            CF.sub.3                                                                               H        COOH salts                                      Cl            Cl      H        H                                               Cl            Cl      H        OCH.sub.3                                       Cl            Cl      H                                                                                        ##STR308##                                     F             CF.sub.3                                                                               Cl       OC.sub.2 H.sub.5                                 ##STR309##                                                                    R                 R.sub.1          R.sub.2                                     __________________________________________________________________________     tert.-C.sub. 4 H.sub.9                                                                           NH.sub.2         SCH.sub.3                                   tert.-C.sub. 4 H.sub.9                                                                            ##STR310##      SCH.sub.3                                    ##STR311##                                                                     ##STR312##                                                                    R              R.sub.1   R.sub.2                                                                               R.sub.3                                        __________________________________________________________________________      ##STR313##    sec -C.sub.4 H.sub.9                                                                     H      H                                              H              CH.sub.3  H      H salts, esetrs                                H              sec -C.sub.4 H.sub.9                                                                     H      H salts, esters                                 ##STR314##    tert.-C.sub.4 H.sub.9                                                                    H      H                                               ##STR315##                                                                     ##STR316##                                                                     ##STR317##                                                                    R             R.sub.1 R.sub.2 X                                                __________________________________________________________________________     CH.sub.3      CH.sub.3                                                                               H       CH.sub.3 OSO.sub.2 O                             CH.sub.3      CH.sub.3                                                                               Br      CH.sub.3 OSO.sub.2 O                             CH.sub.3      CH.sub.3                                                                               CH.sub.3                                                                               CH.sub.3 OSO.sub.2 O                              ##STR318##                                                                     ##STR319##                                                                     ##STR320##                                                                    R          R.sub.1   R.sub.2        R.sub.3                                    __________________________________________________________________________     H          n-C.sub.3 H.sub.7                                                                        CH.sub.2CHCH.sub.2                                                                            CH.sub.3                                   Na         n-C.sub.3 H.sub.7                                                                        CH.sub.2CHCH.sub.2                                                                            CH.sub.3                                    ##STR321##                                                                     ##STR322##                                                                     ##STR323##                                                                     ##STR324##                                                                    R         R.sub.1                                                                              R.sub.2                                                                              R.sub.3                                                                               R.sub.4                                           __________________________________________________________________________     Cl        H     Cl    OCH.sub.3                                                                             H salts, esters, amides                           Cl        Cl    H     Cl     H . (CH.sub.3).sub.2 NH                            ##STR325##                                                                    R                   R.sub.1 R.sub.2                                            __________________________________________________________________________      ##STR326##         CH.sub.3                                                                               H salts, esters, amides                             ##STR327##         H       H salts, esters, amides                             ##STR328##         H       H salts, esters, amides                             ##STR329##         H       H salts, esters, amides                             ##STR330##         CH.sub.3                                                                               H salts, esters, amides                             ##STR331##         CH.sub.3                                                                               H salts, esters, amides                             ##STR332##                                                                    R                            R.sub.1                                           __________________________________________________________________________      ##STR333##                  H salts, esters, amides                            ##STR334##                  H salts, esters, amides                            ##STR335##                                                                     ##STR336##                                                                     ##STR337##                                                                     ##STR338##                                                                     ##STR339##                  salts, esters                                      ##STR340##                                                                     ##STR341##                                                                     ##STR342##                  salts                                              ##STR343##                                                                     ##STR344##                  salts, esters, amides                             __________________________________________________________________________

It is also possible to apply the new compounds according to the invention, either alone or in combination with other herbicides, in admixture with other crop protection agents, e.g., agents for combatting pests or phytopathogenic fungi or bacteria. Of interest is also the fact that the compounds according to the invention may be mixed with mineral salt solutions used to eliminate nutritional and trace element deficiencies.

To ensure that the herbicidal action sets in, spreader-stickers and non-phytotoxic oils may be added.

Application may be effected for instance in the form of directly sprayable solutions, powders, suspensions (including high-percentage aqueous, oily or other suspensions), dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. The forms of application depend entirely on the purpose for which the agents are being used; in any case they should ensure a fine distribution of the active ingredient.

For the preparation of solutions, emulsions, pastes and oil dispersions to be sprayed direct, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, further coal-tar oils, etc. and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons such as benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives such as methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., and strongly polar solvents such as dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, etc. are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastes, oil dispersions or wettable powders by adding water. To prepare emulsions, pastes and oil dispersions the ingredients as such or dissolved in an oil or solvent may be homogenized in water by means of wetting or dispersing agents, adherents or emulsifiers. Concentrates which are suitable for dilution with water may be prepared from active ingredient, wetting agent, adherent, emulsifying or dispersing agent and possibly solvent or oil.

Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acids, phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkyl sulfonates, alkali metal and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, alkali metal and alkaline earth metal salts of fatty acids, salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of sulfated fatty alcohol glycol ether, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol polyglycol ethers, tributylphenol polyglycol ethers, alkylaryl polyester alcohols, isotridecyl alcohols, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulfite waste liquors and methyl cellulose.

Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silicic acid, silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain flours, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.

The formulations contain from 0.1 to 95, and preferably 0.5 to 90, % by weight of active ingredient.

EXAMPLE 9

90 parts by weight of compound 1 is mixed with 10 parts by weight of N-methyl-α-pyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.

EXAMPLE 10

20 parts by weight of compound 1 is dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide to 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

EXAMPLE 11

20 parts by weight of compound 1 is dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide to 1 mole of isooctylphenol, and 20 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

EXAMPLE 12

20 parts by weight of compound 1 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210° and 280° C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

EXAMPLE 13

20 parts by weight of compound 1 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of a ligninsulfonic acid obtained from a sulfite waste liquor, and 60 parts by weight of powdered silica gel, and triturated in a hammer mill. By uniformly distributing the mixture in 20,000 parts by weight of water, a spray liquid is obtained containing 0.1% by weight of the active ingredient.

EXAMPLE 14

3 parts by weight of compound 1 is intimately mixed with 97 parts by weight of particulate kaolin. A dust is obtained containing 3% by weight of the active ingredient.

EXAMPLE 15

30 parts by weight of compound 1 is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.

EXAMPLE 16

40 parts by weight of compound 1 is intimately mixed with 10 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water to give a stable aqueous dispersion. Dilution in 100,000 parts by weight of water gives an aqueous dispersion containing 0.04 wt% of active ingredient.

EXAMPLE 17

20 parts of compound 1 is intimately mixed with 2 parts of the calcium salt of dodecylbenzenesulfonic acid, 8 parts of a fatty alcohol polyglycol ether, 2 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtained. 

We claim:
 1. A compound of the formula ##STR345## where R¹ is alkyl of 1 to 20 carbon atoms, lower haloalkyl, cycloalkyl of 3 to 7 carbon atoms, alkenyl of 2 to 11 carbon atoms, alkynyl of 2 to 8 carbon atoms, lower haloalkenyl, lower haloalkynyl, lower alkoxyalkyl, lower alkylmercaptoalkyl, lower alkyl- and dialkylcarbamoylalkyl, lower alkoxycarbonyl, lower alkoxycarboalkyl, lower alkoxycarboalkenyl, lower alkanoylalkyl, phenyl, phenyl substituted by halogen, methyl or halomethyl, or pyrrolidinyl,R² is CN, SCN, ##STR346## C(═N--OR⁴)R³, S(═O)OR³, S(═O)₂ OR³, Si(R⁶)₂ R⁷, ##STR347## or SCCl₂ F, X is halogen, NO₂, lower alkyl, halo lower alkyl, cycloalkyl, benzyl, phenyl, CN, SCN, CO₂ R³, ##STR348## Y'R⁴, SO₂ R³, SO₂ OR³, ##STR349## CCl₃, CF₃, C(═O)R³ or Y"CF₂ C(Z)₃, R³ is hydrogen, lower alkyl, phenyl, or phenyl substituted by halogen, methyl or nitro, R⁴ and R⁵ being identical or different and each having the meanings of R³ and are additionally, but not simultaneously, lower alkanoylalkyl, R⁶ and R⁷ being identical or different and each having the meanings of R³ with the exception of hydrogen, R⁸ and R⁹ being identical or different and each having the meanings of R³ with the exception of hydrogen and phenyl, A having the meanings of R³ or is OR³, N(R³)₂, OC(═O)NHR³ or OC(═O)R³, each Y, Y' and Y" is independently hydrogen, oxygen or sulfur, each Z is independently hydrogen, fluorine, bromine, chlorine or iodine, m is one of the integers 0, 1, 2, 3 and 4, and n is the integer
 2. 2. 1-Cyano-3-n-propyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide.
 3. 1-Cyano-3-isopropyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide.
 4. 1-Cyano-3-sec-butyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide.
 5. 1-Cyano-3-cyclohexyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide.
 6. 1-Cyano-3-β-chloroethyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide.
 7. 1-Cyano-3-isopropyl-8-methyl-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide.
 8. 1-Cyano-3-isopropyl-6-bromo-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide.
 9. 1-Cyano-3-isopropyl-8-chloro-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide.
 10. 1-Cyano-3-isopropyl-8-methoxy-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide
 11. 1-Cyano-3-isopropyl-8-fluoro-2,1,3-benzothiadiazin-(4)-one-2,2-dioxide.
 12. A process for controlling the growth of unwanted plants which comprises treating the plants or soil with a compound of the formula ##STR350## where R¹ is alkyl of 1 to 20 carbon atoms, lower haloalkyl, cycloalkyl of 3 to 7 carbon atoms, alkenyl of 2 to 11 carbon atoms, alkynyl of 2 to 8 carbon atoms, lower haloalkenyl, lower haloalkynyl, lower alkoxyalkyl, lower alkylmercaptoalkyl, lower alkyl- and dialkylcarbamoylalkyl, lower alkoxycarbonyl, lower alkoxycarboalkyl, lower alkoxycarboalkenyl, lower alkanoylalkyl, phenyl, phenyl substituted by halogen, methyl or halomethyl, or pyrrolidinyl,R² is CN, SCN, ##STR351## C(═N--OR⁴)R³, S(═O)OR³, S(═O)₂ OR³, Si(R⁶)₂ R⁷, ##STR352## or SCCl₂ F, X is halogen, NO₂, lower alkyl, halo lower alkyl, cycloalkyl, benzyl, phenyl, CN, SCN, CO₂ R³, ##STR353## Y'R⁴, SO₂ R³, SO₂ OR³, ##STR354## CCl₃, CF₃, C(═O)R³ or Y"CF₂ C(Z)₃, R³ is hydrogen, lower alkyl, phenyl, or phenyl substituted by halogen, methyl or nitro, R⁴ and R⁵ being identical or different and each having the meanings of R³ and are additionally, but not simultaneously, lower alkanoylalkyl, R⁶ and R⁷ being identical or different and each having the meanings of R³ with the exception of hydrogen, R⁸ and R⁹ being identical or different and each having the meanings of R³ with the exception of hydrogen and phenyl, A having the meanings of R³ or is OR³, N(R³)₂, OC(═O)NHR³ or OC(═O)R³, each Y, Y' and Y" is independently hydrogen, oxygen or sulfur, each Z is independently hydrogen, fluorine, bromine, chlorine or iodine, m is one of the integers 0, 1, 2, 3 and 4, and n is the integer
 2. 